14199-15-6

Basic information

• Product Name: Methyl 4-hydroxyphenylacetate
• Synonyms: METHYL 4-HYDROXYPHENYLACETATE;METHYL P-HYDROXYPHENYL ACETATE;4-HYDROXYPHENYLACETIC ACID METHYL ESTER;4-hydroxy-benzeneaceticacimethylester;Acetic acid, (p-hydroxyphenyl)-, methyl ester;p-Hydroxyphenylacetic acid methyl ester;Methyl 4-hydroxyphenylacetate 99%;Methyl 4-hydroxyphenylacetate, 98+%
• CAS NO: 14199-15-6
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 238-050-2
• Product Categories: Aromatic Esters;C8 to C9;Carbonyl Compounds;Esters;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;pharmaceutical
• Mol File: 14199-15-6.mol
• Article Data: 74

Chemical Properties

• Melting Point: 55-58 °C(lit.)
• Boiling Point: 162-163 °C5 mm Hg(lit.)
• Flash Point: 163°C/5mm
• Appearance: White to pale yellow/Crystals
• Density: 1.1708 (rough estimate)
• Vapor Pressure: 0.000189mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol
• PKA: 9.72±0.13(Predicted)
• BRN: 2087538
• CAS DataBase Reference: Methyl 4-hydroxyphenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-hydroxyphenylacetate(14199-15-6)
• EPA Substance Registry System: Methyl 4-hydroxyphenylacetate(14199-15-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 14199-15-6(Hazardous Substances Data)

Usage

Description

Methyl 4-hydroxyphenylacetate, also known as 4-(2-hydroxy-3-isopropylamino)propoxyphenylacetic acid, is a methyl ester derived from the formal condensation of the carboxy group of 4-hydroxyphenylacetic acid with methanol. It has been isolated from Penicillium chrysogenum and is characterized by its white to pale yellow crystalline appearance. Methyl 4-hydroxyphenylacetate is known for its ability to inhibit the activity of the tobacco mosaic virus (TMV).

Uses

Used in Pharmaceutical Industry:
Methyl 4-hydroxyphenylacetate is used as an intermediate in the synthesis of various pharmaceutical compounds. It plays a crucial role in the production of 4-(2-hydroxy-3-isopropylamino)propoxyphenylacetic acid, which has potential applications in the development of new drugs.
Used in Agricultural Industry:
In the agricultural sector, Methyl 4-hydroxyphenylacetate is utilized for its antiviral properties. It is employed as an inhibitor of the tobacco mosaic virus (TMV), helping to protect plants from viral infections and ensuring a healthy crop yield.
Used in Chemical Research:
Due to its unique chemical structure and properties, Methyl 4-hydroxyphenylacetate is also used in chemical research for studying various reactions and exploring its potential in the synthesis of other organic compounds. This contributes to the advancement of knowledge in the field of organic chemistry and the development of new applications for this compound.

InChI:InChI=1/C9H10O3/c1-12-9(11)6-7-2-4-8(10)5-3-7/h2-5,10H,6H2,1H3

Upstream product

• 67-56-1 methanol 
• 156-38-7 4-hydroxyphenylacetate 
• 2065-23-8 methyl 2-phenoxyacetate 
• 143-33-9 sodium cyanide 
• 824-94-2 p-methoxybenzyl chloride 
• 186581-53-3 diazomethane 
• 14191-95-8 4-cyanomethylphenol 
• 20667-76-9 3-methyl-1-p-tolyltriazene 
• 112211-78-6 [4-(2-Formyl-benzenesulfonyloxy)-phenyl]-acetic acid methyl ester 
• 101-41-7 benzeneacetic acid methyl ester 
• 188119-50-8 diethyl (2-(4-hydroxyphenyl)-2-oxoethyl) phosphate 
• 20816-46-0 α,α-dimethyl-p-hydroxyphenacyl acetate 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 
• 1445-45-0 Trimethyl orthoacetate 

Downstream Products

• 14383-18-7 (4-hydroxy-phenyl)-acetic acid-(4-benzyloxy-3-methoxy-phenethylamide) 
• 34918-57-5 methyl 3-bromo-4-hydroxyphenylacetate 
• 212688-02-3 3,5-dibromo-4-hydroxyphenylacetic acid methyl ester 
• 20277-02-5 2-(4-hydroxyphenyl)acetatic acid hydrazide 
• 100798-56-9 (3,3-diacetoxy-4-oxo-cyclohexa-1,5-dienyl)-acetic acid methyl ester 
• 35400-15-8 4-acetoxyphenylacetic acid methyl ester 
• 29112-35-4 (4-hydroxy-phenyl)-acetic acid allylamide 
• 64360-35-6 [4-(4-Methoxy-3-methyl-benzyloxy)-phenyl]-acetic acid 
• 69182-95-2 {4-[3-(4-Chloro-phenoxy)-propoxy]-phenyl}-acetic acid methyl ester 
• 64360-36-7 [4-(4-Isopropoxy-3-methyl-benzyloxy)-phenyl]-acetic acid 
• 69183-35-3 {4-[2-(4-Chloro-phenoxy)-propoxy]-phenyl}-acetic acid methyl ester 
• 64360-37-8 [4-(3-Chloro-4-isopropoxy-benzyloxy)-phenyl]-acetic acid 
• 69182-88-3 {4-[2-(4-Chloro-phenoxy)-ethoxy]-phenyl}-acetic acid methyl ester 
• 69182-74-7 [4-(4-Chloro-phenoxymethoxy)-phenyl]-acetic acid methyl ester 

Relevant articles and documents

Fe(III)-Catalyzed Aromatic Hydroxylation with H2O2 in the Presence of a Variety of Electron-Transfer Agents

Electron-transfer agents such as N,N,N',N'-tetramethylphenylenediamine (TMPD), ferrocenes, and phenothiazines have been found to mediate the hydroxylation of benzene with H2O2 in the presence of Fe3+.Of these, TMPD catalyst is the most effective to provide phenol in 80percent or better yield based on added H2O2 under the optimized conditions.A general mechanism, involving the rate-determining reduction of Fe3+ to Fe2+ with such mediators, is suggested.

Synthesis and characterization of a novel Mn(III)-(γ-diketone) complex with catalytic and antifungal activity

A novel Mn(III) complex with γ-diketone having general formula [Mn(hdo)3], where hdo = hexane-2,5-dione ligand, has been synthesized and characterized using UV–vis, FT-IR, ESI-mass and EPR spectra, elemental analysis, powder X-ray diffraction, SEM, and magnetic susceptibility measurements. The X-ray diffraction studies reveal that it has monoclinic lattice system with C2/C space group and the unit cell dimensions are a = 9.92245 ?, b = 10.50696 ?, and c = 9.80835 ?. The particle size of this complex has been found to be 32.1 nm. The complex was evaluated for its antifungal activity against Aspergillus flavus, Aspergillus niger, and Aspergillus terreus fungal species. The results indicate that the minimum inhibitory concentration of the synthesized complex was 8 ppm for A. niger while for A. flavus and A. terreus it was 6 ppm. β-Diketone Mn(III) complexes inhibit the fungal growth only partially. This communication is the first report of transformation of a keto-group to an ester group catalyzed by a metal complex.

Identification and Profiling of a Novel Diazaspiro[3.4]octane Chemical Series Active against Multiple Stages of the Human Malaria Parasite Plasmodium falciparum and Optimization Efforts

A novel diazaspiro[3.4]octane series was identified from a Plasmodium falciparum whole-cell high-throughput screening campaign. Hits displayed activity against multiple stages of the parasite lifecycle, which together with a novel sp3-rich scaffold provided an attractive starting point for a hit-to-lead medicinal chemistry optimization and biological profiling program. Structure-activity-relationship studies led to the identification of compounds that showed low nanomolar asexual blood-stage activity (50 nM) together with strong gametocyte sterilizing properties that translated to transmission-blocking activity in the standard membrane feeding assay. Mechanistic studies through resistance selection with one of the analogues followed by whole-genome sequencing implicated the P. falciparum cyclic amine resistance locus in the mode of resistance.

Carboxylic Acid Reductase Can Catalyze Ester Synthesis in Aqueous Environments

Most of the well-known enzymes catalyzing esterification require the minimization of water or activated substrates for activity. This work reports a new reaction catalyzed by carboxylic acid reductase (CAR), an enzyme known to transform a broad spectrum of carboxylic acids into aldehydes, with the use of ATP, Mg2+, and NADPH as co-substrates. When NADPH was replaced by a nucleophilic alcohol, CAR from Mycobacterium marinum can catalyze esterification under aqueous conditions at room temperature. Addition of imidazole, especially at pH 10.0, significantly enhanced ester production. In comparison to other esterification enzymes such as acyltransferase and lipase, CAR gave higher esterification yields in direct esterification under aqueous conditions. The scalability of CAR catalyzed esterification was demonstrated for the synthesis of cinoxate, an active ingredient in sunscreen. The CAR esterification offers a new method for green esterification under high water content conditions.

Isolation and structure–activity relationship studies of jacaranones: Anti-inflammatory quinoids from the Cuban endemic plant Jacaranda arborea (Bignoniaceae)

The Cuban endemic plant Jacaranda arborea (Bignoniaceae) has been traditionally used in folk medicine as an acaricide and for acne treatment. Two known quinoids, methyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate (jacaranone) (1) and its ethyl ester 2 were isolated from this species as anti-inflammatory substances. Compound 1 prominently inhibited the production of TNF-α in both LPS-treated macrophages and mice, with low toxicity. Structure-activity relationship studies revealed that the high electrophilicity of 1 as a Michael acceptor played an important role in these effects. Unlike in previous studies, such as those on antitumor, anti-oxidant, and anti-malarial activities, ester derivatives of 1 retained their potent anti-inflammatory activity. Our results suggest that jacaranones may target specific biomacromolecule(s) at lower concentrations than hitherto expected to exhibit potent activities.